Guapsidial A and Guadials B and C: Three New Meroterpenoids with Unusual Skeletons from the Leaves of Psidium guajava

Chemistry. 2015 Jun 15;21(25):9022-7. doi: 10.1002/chem.201500533. Epub 2015 May 12.

Abstract

A novel sesquiterpene-based Psidium meroterpenoid, possessing an unusual coupling pattern, and two new monoterpene-based meroterpenoids with unprecedented skeletons were isolated from the leaves of Psidium guajava. Their structures and absolute configurations were elucidated by spectroscopic, X-ray diffraction, and computational methods. The plausible biosynthetic pathway of these meroterpenoids as well as their cytotoxicities toward HepG2 and HepG2/ADM cells were also discussed.

Keywords: biogenetic pathways; cytotoxicity; meroterpenoids; natural products; structure elucidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry*
  • Biological Products / isolation & purification
  • Hep G2 Cells / chemistry
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry*
  • Psidium / chemistry*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / isolation & purification
  • Sesterterpenes / chemistry*
  • Sesterterpenes / isolation & purification
  • X-Ray Diffraction

Substances

  • Biological Products
  • Sesquiterpenes
  • Sesterterpenes
  • guadial B
  • guadial C
  • guapsidial A